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5-Benzoyl-4-benzyl-1-(2-hydroxyethyl)-2-(pyrrolidine-1-carbonyl)-3b,4,5,6,6a,7-hexahydro-
1H-1,5-diazacyclopenta[a]pentalene-4-carboxylic acid methyl ester (308h). Prepared by
following general procedure T with: 307 (50 mg, 0.097 mmol), ethanolamine (18 µL, 0.29
mmol), AcOH (100 µL). Yield 308h (42 mg, 80%).
1 H NMR (300 MHz, CDCl3): δ 7.48-7.40 (m, 5H), 7.36-7.30 (m, 5H), 6.26 (s, 1H), 4.23 (d, J =
13.6 Hz, 1H), 4.18-4.09 (m, 2H), 3.88 (d, J = 7.4 Hz, 1H), 3.80 (t, J = 5.1 Hz, 1H), 3.75-3.57 (m,
4H), 3.64 (s, 3H), 3.39 (d, J = 13.7 Hz, 1H), 3.37-3.20 (m, 2H), 2.57 (dd, J = 15.3, 8.1 Hz, 1H),
2.41-2.31 (m, 1H), 2.25 (d, J = 15.4 Hz, 1H), 2.03-1.90 (m, 4H); 13 C NMR (75 MHz, CDCl3): δ
172.2, 169.7, 162.0, 141.3, 137.5, 137.0, 131.0, 129.7, 129.6, 128.4, 128.2, 126.8, 126.3, 123.2,
109.3, 72.9, 62.6, 56.2, 52.1, 52.0, 49.9, 48.8, 46.7, 45.6, 39.2, 28.6, 26.5, 24.1; IR (thin film): ν
3394, 2949, 1734, 1600, 1448, 1402 cm -1 ; MS m/z (%) 541 (45), 482 (13), 450 (54), 379 (28),
328 (20), 105 (100); EI-HRMS calcd for C32H35N3O5 m/z [M] + 541.2577; found 541.2574.
H
BzN
MeO2C Bn
H
5-Benzoyl-4-benzyl-1-(2-methoxyethyl)-2-(pyrrolidine-1-carbonyl)-3b,4,5,6,6a,7-
308i
hexahydro-1H-1,5-diazacyclopenta[a]pentalene-4-carboxylic acid methyl ester (308i).
Prepared by following general procedure T with: 307 (35 mg, 0.068 mmol), 2-
methoxyethylamine (18 µL, 0.20 mmol), AcOH (80 µL). Yield 308i (35 mg, 93%).
1 H NMR (300 MHz, CDCl3): δ 7.44-7.27 (m, 10H), 6.23 (s, 1H), 4.32 (dt, J = 14.1, 4.9 Hz, 1H),
4.23 (d, J = 13.6 Hz, 1H), 4.07 (dt, J = 14.1, 5.0 Hz, 1H), 3.88 (d, J = 7.4 Hz, 1H), 3.70-3.51 (m,
9H), 3.40 (d, J = 13.7 Hz, 1H), 3.37-3.31 (m, 1H), 3.21 (s, 3H), 3.21-3.15 (m, 1H), 2.58 (dd, J =
15.6, 7.0 Hz, 1H), 2.33-2.26 (m, 1H), 2.25 (d, J = 16.0 Hz, 1H), 2.00-1.90 (m, 4H); 13 C NMR (75
MHz, CDCl3): δ 172.3, 169.7, 161.9, 141.8, 137.6, 137.0, 131.0, 129.5, 129.0, 128.3, 128.1,
272
N
O
O
N